تفاعل #657334

ord-92a8b32be51c464ba385f2f4b6fddb48

معادلة التفاعل

CCOC(=O)CBr
ethyl bromoacetate
O=[N+]([O-])c1cc(Br)ccc1O
4-bromo-2-nitro-phenol
O=C([O-])[O-].[K+].[K+]
potassium carbonate
CCOC(=O)COc1ccc(Br)cc1[N+](=O)[O-]
product
المردود 77.0%
CCOC(=O)COc1ccc(Br)cc1[N+](=O)[O-]
(4-Bromo-2-nitro-phenoxy)-acetic acid ethyl ester
المردود 77.0%

الكواشف

لا شيء

المذيبات

ظروف التفاعل

درجة الحرارة
60°CELSIUS
الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

  1. 1
    درجة الحرارةthen cooled to 23° C
  2. 2
    أخرىThe reaction mixture was partitioned between ethyl acetate:heptane (1:1) and water (100 mL each)
  3. 3
    أخرىThe organic layer was separated
  4. 4
    غسيلwashed successively with water, saturated brine solution (100 ml
  5. 5
    تجفيفeach) then dried (MgSO4)
  6. 6
    ترشيحfiltered
  7. 7
    تركيزconcentrated

الإجراء التجريبي

To a solution of 4-bromo-2-nitro-phenol (3.28 g, 15.0 mmol, 1 equiv) in dimethylformamide (40 mL) at 23° C. was added potassium carbonate (4.14 g, 30 mmol, 2 equiv) followed by ethyl bromoacetate (1.84 mL, 16.6 mmol, 1.1 equiv). The resulting mixture was warmed to 60° C. (oil bath) for 90 min then cooled to 23° C. The reaction mixture was partitioned between ethyl acetate:heptane (1:1) and water (100 mL each). The organic layer was separated and washed successively with water, saturated brine solution (100 ml, each) then dried (MgSO4), filtered and concentrated to give 4.50 g (11.5 mmol, 77%) of the product as a yellow oil.

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: US09023843B2uspto-grants-2015_05